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. 2017 Oct 9;56(42):13130-13134.
doi: 10.1002/anie.201707070. Epub 2017 Sep 12.

Ligand-Controlled Regiodivergent and Enantioselective Copper-Catalyzed Hydroallylation of Alkynes

Guoxing Xu  1 , Haiyan Zhao  1 , Bin Fu  1 , Aijie Cang  1 , Ge Zhang  1 , Qian Zhang  1 , Tao Xiong  1 , Qian Zhang  1
Affiliations

Ligand-Controlled Regiodivergent and Enantioselective Copper-Catalyzed Hydroallylation of Alkynes

Guoxing Xu et al. Angew Chem Int Ed Engl. .

Abstract

A ligand-controlled regiodivergent and enantioselective copper-catalyzed intermolecular hydroallylation of alkynes with allylic phosphates and hydrosilanes has been achieved for the first time. The chiral bidentate sulfonate-containing N-heterocyclic carbene ligated CuCl complex leads to enantioenriched SN 2'-type products, whereas the use of the IMesCuCl catalyst affords SN 2-type products. Thus a range of chiral branched and achiral linear 1,4-dienes could be facilely synthesized from readily available alkynes in a regiodivergent manner.

Keywords: N-heterocyclic carbenes; alkynes; allylic compounds; copper; enantioselectivity.

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